A Gift in Disguise Ch. 01

I nodded.

"So did you ever buy copies of sexually provocative magazines like Playboy or Penthouse?"

"No, mom and dad wouldn't allow them in the house. Besides, it was a small town, and none of the stores had them. I never even saw Playboy until I went to a friend's house. He had the centerfold pictures up on his bedroom wall."

"How often did you masturbate in high school, Tom?"

"Every day, sometimes twice a day. Whenever I felt like it and could be alone."

"So you never masturbated with other boys around?"

"No."

"And you never masturbated in a public place, especially where a girl might see you?"

"No."

"And you always just used magazines to stimulate you?"

"Yeah. Well, no, not exactly. Sometimes I used to fantasize about having sex with the girls in my high school."

"Of course you did. Youíre a good looking man. You were probably as attractive to them in high school as you are now. My guess is that some of them were having similar fantasies about being with you. Although with girls that age, it may have been a more emotional than physical attraction. Were your fantasies limited to the girls you saw every day at school?"

"Pretty much. There was this woman about my mother's age that I thought about."

"Tell me about her, Tom."

"Well, she was about mom's age or maybe a little older. She was really pretty and had a real nice figure. Always wore makeup and nice clothes. She had two son, both older than me, in high school. Anyway, she and her husband would sometimes come to our house after dinner to talk about neighborhood issues with my parents and our neighbors. They would meet in our living room, and I'd be in my room studying.

I happened to look out one night and saw this lady, Sharon, sitting across from my bedroom door. She was wearing a skirt that came up above her knees, and she was wearing stockings. I could look right up her skirt. That really turned me on. It was kind of strange at the time."

"What was strange about it, Tom?"

"The very first night that happened, she caught me looking up her skirt. I figured she'd tell mom and I'd get in trouble. But that didn't happen. Not only that, every time they'd come back for another meeting, she'd wear a skirt and sit in exactly the same chair. I'd look out, look up her skirt for a while, she'd see me and smile, and I'd quietly close my bedroom door and jack off thinking about her."

"It sounds to me like she was encouraging you to look."

"Yeah, she was," I said emphatically.

"You seem pretty sure of that. How do you know?"

"Because during the summer between high school and my first year of college, her boys invited me to spend a Saturday water skiing and swimming at their lake place. I showed up at their cabin, but only Sharon was there. She said her husband and the boys had gone across the lake for ice cream but would be back before long. She was wearing a one-piece swimsuit with a wraparound skirt, and I started getting turned on.

We started talking, and eventually she mentioned seeing me looking up her skirt. Well, I was pretty embarrassed, but she said not to worry, that she was actually flattered that a good looking young man thought her legs were pretty. I was kind of tongue-tied and didn't say anything. Then she asked if Iíd like to get a better look at her legs.

She didn't wait for me to answer. She stood up and peeled off the wraparound skirt. She was standing in front of me with only her swimsuit on. She really had a great body for someone her age. Well, I started getting a hard-on. Sorry about the language."

"Don't worry about your language, Tom. Go on, please."

"Okay. She said that since she had shown me her body, I should show her mine. She asked if I had my swimsuit on under my pants, and when I said I did, she started taking off first my shirt, then my pants. I was left standing in front of her in my tight swimsuit and nothing else to hide my erection."

"So what happened then, Tom?"

"She said something like, 'Why, Tom. Am I causing that?' and she stared right at the bulge in my swimsuit. Then she said, 'That must be awfully uncomfortable. Why don't you take off your swimsuit?' I didn't do anything, so she walked over to me and just pulled my trunks down. My cock ... I mean, my penis..."

A dismissive wave from her hand reminded me to use my own words.

"Anyway, my cock popped straight out in front of her face. I didn't quite know what to do, but she reached out and started handling my cock and my balls. Then she stepped back and said, 'You know, Tom, since you don't have anything on, it's only fair that I shouldn't either.' Then she peeled off her swimsuit. I thought I was going to cum right then and there. She had really nice breasts and full hips and a really nice hairy pussy."

I glanced at Dr. Theriault to see if she would rebuke me for my crude language. She didn't bat an eye, so I guessed I could go on.

"Sharon asked me if I liked what I saw, and I just nodded. My mouth was too dry to say anything. She laughed. With two boys of her own, she probably knew exactly how I felt with my cock bobbing up and down.

Then she just walked over to me and started kissing me and rubbing her body all over against mine. I could feel her nipples rubbing against my chest. She kissed me really hard, so I kissed her back just as hard. She was straddling my upper thigh, and I could feel her rubbing her pussy up and down on it. She seemed to really enjoy that. She kept humping my leg harder and faster. Then she started gasping and dug her fingernails into my back.

I pushed her toward the couch. When I did that she said she really got turned on by a man who knew what he wanted and wouldn't stop until he got it. She draped one of her legs over the back of the couch so I could see her pussy opening better. Well, by then I was ready to fuck her, so I got on top of her and started to put my cock into her.

Just then, there was a loud roar outside. It was their boat's engine. Her husband and boys were back from getting ice cream. She pushed me off and said, 'Shit! They're back. Get dressed. Quick!' We both got our clothes back on just before they came inside."

"So if they had not returned, it's likely you would have fucked her? Is that right, Tom?"

I was surprised at how naturally Dr. Theriault said 'fuck.'

"I never really thought about that, but yeah, I guess."

"And that happened during the summer between high school and college, right?"

"Um-hm."

"Let's go back a little bit. How old were you when you first started dating?"

It took a long time for me to answer.

"I never really dated much until my senior year in high school. See, I was kind of the brain, not really the jock type the girls wanted to be with."

"How did you come to that conclusion, Tom?"

"I don't know. That's just the way it seemed to me."

"All right. So in your senior year you started to date a bit more?"

"Yeah. I kind of liked this one girl in my class. She was smart, pretty in a nice sort of way. Very nice. She didn't date much, either. Her father was the pastor at our church. Mom and dad wanted me to date her. I guess they thought she was safe, that she wouldn't encourage me sexually. Boy, were they wrong."

"How were they wrong, Tom?"

"Well, she and I had just turned 18, so I already had my drivers license. The first time we dated was to go to a school dance. I picked her up, we went to the dance, and I took her home. Nothing happened. Not even a goodnight kiss. I did ask her if she'd like to go to a movie some time. She said she would. She said a movie she really wanted to see was coming to the drive-in in Wilsonville next week. Wilsonville was 20 miles away, but I asked her to go with me if I could get the car. I went home and asked dad if I could take her, and he said I could."

"Go on."

"The next Friday night I picked her up and we drove to the drive-in theater. The parking lot lights went down and the cartoon came up on the screen. She scooted over next to me and put her head on my shoulder. I was a little surprised, but I put my arm around her shoulder and pulled her even closer. When the movie started, she reached up, put her hand on my cheek, and turned my head toward her. Then she kissed me. Then I kissed her back. Harder. Before long, we had forgotten about the movie and were kissing like crazy. I felt her push her tongue between my lips and into my mouth. It felt good, so I did the same thing to her. I felt my cock getting hard. Then she put her hand on it and started rubbing it through my pants. That made it real hard. She seemed to like that, so she kept rubbing while we kissed. I started to put my left hand on her breast, but she gently pushed it away. She said, 'Not yet', but she kept kissing and rubbing me. Then she asked me, 'Are you close?' I said, 'Close to what?', and she said, 'Close to cumming, silly,' with a little giggle. I said I was. Then she stopped rubbing me, unfastened my belt, released the clasp on my pants, and unzipped them. She reached into my pants, took hold of my cock, and pulled it out. I was a little scared that someone might see us. She reached for a blanket in the back seat and put it over us so no one could see what was going on under the blanket. Well, I figured maybe she was going to jack me off, but she didn't. Instead, we kept kissing each other, getting hotter and hotter. Then she took my hand and put it back on her breast. I unbuttoned her blouse and slipped my hand inside it. She said, 'Wait a sec.' Then she slipped away from me, took her blouse off, and removed her bra. I just stared at her tits...I mean, her breasts, under the blanket."

"Tom, I'm familiar with 'tits.' I have two of them."

"She scooted back next to me and put my left hand on her right breast. Her nipple was real hard. We kept kissing, I played with her tit, and she played with my cock. All of this was going on under the blanket. I was about ready to cum. I guess she was, too, because she was breathing a lot harder now. Then she took my hand from her breast and put it down on her thigh just below her skirt. While we were kissing, I moved my hand up to her underpants. I started rubbing her the same way she had been rubbing me. We were still kissing and stuff, and she was rubbing her tits against me now, and her hand was still trying to stroke my cock. Then a funny thing happened. She started talking real dirty to me."

"How do you mean 'dirty,'Tom? What was she saying?"

"Things like, 'Rub my pussy faster, Tommy! Make me cum for you!' She said it again and again. I never thought the pastor's daughter would say something like that."

"And..."

"And she kept stroking my cock. Now she was pumping it really hard. I just kind of slipped my hand up under her panties and felt her pussy. It was wet and warm, and real hairy. I wasn't quite sure what to do. She must have sensed that, because she said something like, 'Put your finger inside me, baby, like it was your cock.' I did. It felt like one of those Chinese finger trap puzzles when she clamped down around my finger. I slipped it in and out of her wet pussy. She started moaning, pretty loud actually, telling me to fuck her and make her cum. We were still trying to kiss, and she was stroking me, but it was pretty awkward. I started saying dirty things to her, and when I did, she really started humping against my hand and stroking me.

It didn't take long. I came first, real hard, shooting my cum all over the underside of the blanket that was covering us. I felt her bucking against my hand. Her face was all tight and pinched, then she just gave out a loud long growl, and collapsed back into the seat. We were both gasping for breath. We waited until we had caught our breath. Then she pulled several tissues from the box in the back seat and used them to clean me off and clean my cum off the blanket and off my pants. I started getting hard again when she was cleaning me off. I told her I'd really like to fuck her, but she said no, that she wanted to be a virgin when she got married. But she let me feel her tits again, and she did jack me off again."

"So how many dates did you have with Linda where you and she mutually masturbated each other?"

"Quite a few. Then she started dating a college student that she knew. They got married within a year I think."

"Tom, if she would have let you, do you think you could have fucked her?"

"Yeah, I think so. I mean, each time I was rock hard and ready to fuck her silly. Oops, sorry Lorraine."

"You don't have to apologize for using sexually explicit language with me, Tom. I'm completely sure you don't use it in social settings where it would be inappropriate, but it is perfectly appropriate here. In fact, I think it's quite therapeutic for you. That's part of your opening up to me. Please use the words that are easy for you to use, and don't worry about making me uncomfortable.

So in a fairly short period of time, you and Linda mutually masturbated at least five times. And am I correct in assuming you both enjoyed it?"

"Oh, yeah, for sure." I answered.

"Tell me, Tom, were you ever nervous about letting her see your cock and stroke it?"

"Maybe the first time, yeah. But she really seemed to enjoy it, especially when I would cum hard. And I know we both were satisfied when I rubbed her pussy. So after being a little shy or modest or something the first time, it didn't bother me at all. Actually, I looked forward to it."

"But you never tried to force her to let you fuck her, right?"

"No. It's not that I didn't want to; I did. And I tried to persuade her to let me, but she really didn't want to. Since we were both having such a good time masturbating each other, I didn't want to spoil that. Neither did she."

"So Linda seemed to enjoy having you masturbate her. I'm curious, Tom. How exactly were you doing it? What was your technique that was so satisfying to her?"

I felt my face getting hot again, and Dr. Theriault noticed.

"Don't be embarrassed, Tom. It sounds as if you were doing something that really pushed her buttons and sexually satisfied her. That's important. It sounds like you are sexually unselfish. So what exactly did you do to her?"

"Well, she helped at first. She told me to slow down and just touch around her pussy lightly. She said not to rub her too hard. There was this one time when instead of my touching her clit, I just pressed her own pussy lips tight around it. She came so fast and so hard when I did that I thought I had hurt her. I hadn't, though. After that, that's how she wanted me to jerk her off -- by pushing her skin tight around her clit and then moving my hand from side to side and up and down just a little. I didn't even have to touch her clit myself. She was doing something at the same time with some muscles in her pussy..."

"They're the pubococcygeal muscles, sometimes called the Kegel muscles, Tom. What she was doing was using her Kegels to increase the friction on her clit. She was actually helping you jerk her off, and she was increasing her own pleasure at the same time. It is a very effective way for a woman to help her partner satisfy her without actually penetrating her. When I use a vibrator dildo, I use my Kegels to grip it. I come much harder that way."

The look on my face when she talked about using a dildo may have amused Dr. Theriault.

"What, Tom? Does it bother you to think that I actually use a dildo sometimes for sexual pleasure?"

The way she asked did not suggest she had been offended.

"Um, no, not exactly. To tell you the truth, Doc..."

"Please, Tom ... Lorraine."

"Actually, Lorraine, it kind of turns me on."

"Well, thank you, Tom," she said sincerely. "It's nice to know I can still excite a virile young man. And I'm very happy you can communicate so honestly with me. So, is there anything else you would like to tell me about your masturbation sessions with Linda?"

I thought for a while, then said, "Well, there was something kind of strange happened the very last time we were together."

I paused, not sure if I really should go on. Dr. Theriault didn't wait.

"What was so strange, Tom?"

"Well, we had been kissing and stuff, and I put my finger up her pussy like I had done before. But this time I touched her clit with the tip of my thumb, sort of like I was trying to touch the tip of my middle finger with it. Just at that instant, she was still jerking me off, I came real, real hard."

"And..."

"Her eyes flew open, and she started thrashing around real hard. Then she started screaming real loud. I thought I had hurt her, so I stopped, but she just glared and me and begged me not to stop. So I did it all over again. She must have cum three or four times in just a couple of minutes. Finally her body just went limp. I thought she had passed out or even died or something. It even seemed like she stopped breathing. I kind of tried to wake her up, you know, by shaking her a little. She opened her eyes and began breathing real hard. Then she got kind of a peaceful but questioning look on her face. When she finally got her breath back enough to talk, she said that she had never felt an orgasm like that before. I asked her if she wanted me to do it again, and she said she didn't think she had the strength for it. She was exhausted, she didn't even have the strength to jack me off again. She just wanted to watch me do myself, so I did."

"And whatever you did that time with Linda -- have you ever used the same technique with any other women, Tom?"

"No, it kind of scared me. I mean, I really thought she might die."

For the first time, Dr. Theriault looked a little puzzled and didn't have a ready explanation.

We talked for a while longer. She asked me to recount other instances when I had tried to penetrate a woman but had been unable to. She elicited that in each case the woman had been less than encouraging. She also suggested that my being a gentleman and stopping when a woman said "no" was perfectly acceptable behavior. Her thought was that I might have been hypersensitive to being rebuked by the women if I had been just a little more assertive. When she explained it the way she did, it didn't sound quite so hopeless.

"Tom, I really want to thank you for being so open with me. I think we should stop for today. Can you come back next Thursday morning?"

"Sure."

"I don't want to get your hopes up, but it seems to me that you have all it takes to complete intercourse with a woman. What we need to do is figure out how we can break down whatever barrier is inhibiting you. The tests I plan to do next Thursday and the following Thursday should help immensely with that. I have some homework for you to do before next Thursday."

"Homework?"

"Yes, starting tomorrow I would like for you to masturbate at least twice daily. I want you to masturbate at least once on Thursday morning before you get here."

She said it as dispassionately as if she was telling me to read three chapters in an English literature book.

"There's more," she continued. "I want you to keep a diary with some information about each masturbation session."

She obviously saw the look of alarm on my face.

"Tom, don't worry. I will be the only one to see it. With each day, you'll need to include the time you masturbated and the duration of each session. In other words, what time did you start and how long did you jack off before you came. I also need some details about your source of stimulation. Were you reading a magazine, watching a video, or fantasizing. If you were fantasizing about having sex with a particular person, include who the person is and an explanation about what attracts you to that person. Finally, Tom, I need you to rate the intensity of your orgasm on a scale of one to ten with ten being the strongest. I know this will be difficult for you, Tom, but it is very important to help me understand what arouses you."